


5 times Dean won and it didn't matter and the 1 time he lost and it did

by orphan_account



Category: Supernatural
Genre: Angst, Angst with a Happy Ending, First Time, First Time Blow Jobs, M/M, Minor Jessica Moore/Sam Winchester, Minor Violence, Sam is a Tease, Smut, Top Dean Winchester/Bottom Sam Winchester
Language: English
Status: Completed
Published: 2017-09-04
Updated: 2017-09-04
Packaged: 2018-12-23 13:41:59
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, Underage
Chapters: 1
Words: 9,139
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11990988
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: To encourage Sam to try harder during training, Dean offers rewards when he wins. As if that will ever happen.





	5 times Dean won and it didn't matter and the 1 time he lost and it did

**Author's Note:**

  * For [](https://archiveofourown.org/gifts).



> Written for Wincest Love Week.

Win 1

Sam threw a half hearted punch at Dean. Dean scoffed and dodged easily. He grabbed Sam’s arm and pulled him off balance and over his foot, making Sam sprawl into the grass face first.

“Come on, dude. You’re not even trying,” Dean taunted. Sam was smaller than Dean, but he was usually quicker, quicker than this at least.

Sam grunted and flipped over quickly but Dean was on him. Dean sat across his legs and pinned his scrawny forearms to the ground on either side of his head.

“What the hell Sam? You’re better than this,” Dean said frustrated. “You PMSing or what?” He let go of Sam’s wrists and got up, holding out a hand to help Sam.

Sam glared at him but took it. “Shut up,” he mumbled when he got his feet under him.

Dean was getting really annoyed with the moody secretive teenager Sam was becoming. There was no way Dean was half that pissy when he was that age.

He sighed.

Dean looked over his little brother. Sam's shoulders were curled defensively and his too long hair fell in his eyes. He knew Sam hated hunting and everything to do with it but they had to be prepared.

“Alright, one more time. If you can get me to the ground, I’ll let you pick the pizza toppings,” Dean offered without real concern. He didn’t have hopes for Sam beating him, he just wanted him to try.

Sam looked up at him finally, squinting in suspicion. “All veggie?”

“Whatever you want.” Dean spread his arms. “But you gotta beat me first.”

Sam came at him then, sending kicks aimed at Dean’s shins and a punch to the gut. Dean almost had to try to block them, sending Sam’s arm flying wide.

Dean caught the next punch, twisting Sam’s arm behind his back and catching his other arm in a half nelson. Sam wiggled, trying to get out of the hold and his ass rubbed against Dean’s crotch. He was only human and he felt his dick start to thicken. The realization made his grip go slack.

Sam was able to pull his arms free and get one under Dean’s ribs, driving the air from his lungs. He grabbed Dean’s arm and tried to throw him over his shoulder.

Dean recovered though and sidestepped. He used the arm around Sam’s body to throw him bodily onto the grass harder than he meant to.

Sam’s breath left him in a huff and he slammed his fist on the ground.

“Damnit!”

“Come on, Sam. That was good. You almost had me.” Dean extended his hand again to help Sam up.

“Only because you spaced out for a second. Were you even trying?” Sam snapped.

Dean cock was still at half mast in his jeans but he wasn't about to admit that or the cause to Sam. “I was just trying to give you half a chance.”

“Well don't.” Sam stalked off back to the motel room. Dean watched him, noting how he was looking less like a kid and more like the broody teenager he was.

Dean sighed and followed Sam.

When he ordered the pizza, it was veggie.

 

Win 2

“Why don't you ever let me drive?” Sam pouted as the walked into the motel room after school. “Dad taught me months ago and he left us with a fake permit last week.”

Dean tossed the keys in the air and caught them. “Cause I'm the one that does all the work on her.” Dean took off his jacket and added. “And you ride the brakes.”

“Do not.” Sam dropped his bag on the desk and started pulling out books. “You just don’t want me to turn off your shit music.”

“Watch your mouth,” Dean said without heat. “Led Zeppelin is classic.”

“Whatever,” Sam huffed.

Dean watched him open a notebook and starting taking notes from a textbook.

He’d only written one line when Dean interrupted. “Tell you what, Sammy. If you can beat me, I’ll let you drive to school tomorrow.”

Sam’s head snapped up, excitement shining on his face. “Really?”

Dean sighed wearily like it was a huge risk. “Yeah, come on.”

Dean led the way to the leaf strewn area behind the motel. People would be able to see them if they looked out the windows but it didn’t matter. They weren’t really doing anything wrong.

“Alright, if you can get me to the ground, you can drive.”

Sam looked down at his ragged sneakers. He widened his stance, putting one foot a little ahead of the other and bent his knees. He brought his hand up in front of him in a defensive position. When he looked back up with a toss of his hair, he nodded.

Dean readied himself.

They sat there for a moment eyeing each other.

Dean moved first, reaching across for Sam’s right shoulder with his right hand. Sam knocked his arm wide as Dean expected but did take the opening. Sam crouched further into his stance.

“Finally learning,” Dean teased with a grin.

Sam didn’t even scowl. He took a step to the side trying to circle around.

Dean mimicked him.

Sam was focused. A ray of fading sun fell across his baggy t-shirt leaving a streak of yellow light across his arms. It caught the golden highlights in the hair hanging in front of multi-colored eyes. They scanned for an opening, watching every shift of Dean’s movements. Dean was confused by the bubbling of nerves in his stomach from the scrutiny.

He was ready for this to be over now. He lunged at Sam, trying to catch him in a headlock. Sam ducked to the side out of the way. He got a foot behind Dean’s knee and pushed.

Dean’s knee buckled and hit the ground. Sam shoved his shoulder throwing him off balance. Dean grabbed the front of Sam’s shirt as he fell. Dean caught himself on one elbow before he hit the ground. Sam landed on all fours next to him. Dean threw himself at Sam, ending up on top of him, holding his shoulders down with his hands.

Sam’s eyes were wide. His face flushed, lips parted as he gasped for air. Dean was a little out of breath too, but they hadn’t actually done much.

Sam just stared at Dean, flicking his tongue out to wet his lips. Dean felt that weird feeling in his stomach again.

“Guess it’s Kasmir and Black Dog for now, Sammy,” Dean said with a smile. “Almost had me though.” He rolled into the leaves next to Sam, shoulders touching.

Sam still didn’t say anything.

Dean turned his head to catch Sam’s profile. His eyes were squeezed shut, lips pressed together, like he was in pain.

Dean shot up. “Hey, did I hurt you?”

“I’m fine.” Sam stood up and walked away.

Dean watched him leave. That was more the reaction he was expecting.

Dean didn’t let Sam drive to school the next day. When Dad called though, telling them to meet him at a truck stop down the highway, he tossed Sam the keys.

 

Win 3

It was Dean’s day off and he was a few beers down. He lounged on the bed, halfway through a fuzzy episode of ER when Sam came back from soccer practice..

He dropped his bag on his bed with barely a grunt of greeting and headed for the bathroom.

Dean ignored him. He ignored the way the jersey was starting to get tight across Sam’s shoulders. He ignored the way the shorts swished against his skinny legs. He definitely ignored the sweat gathering in the hollow of his little brother’s throat. He’d been ignoring Sam a lot recently.

Dean took another swig of beer.

“Hey, I need to borrow the car Friday night,” Sam announced shirtless, sticking his head out of the bathroom.

“Like hell you are,” Dean sputtered, sitting up.

Sam opened the door fully, taking a step out. “Why not?” he said angrily.

“Because I said so.” Dean spun his legs off the bed to face Sam.

Sam closed the distance between them, standing next to the bed. “Why are you such a jerk?”

Sam towered of Dean in this position, so he stood up. It pissed him off to realize even standing, Dean was only barely taller.

“Me? Why are you such a bitch? I said no. Get over it.”

Sam glowered, his eyes going dark. On anyone else, Dean might have been a little scared.

“What if I beat you?”

Dean frowned. Sam was taller than he used to be and putting on muscle. Dean wasn’t as confident he’d win. He couldn’t let Sam know that.

“Fine. Let’s go.” Dean pushed passed Sam, knocking their shoulders together hard.

He heard Sam sigh and knew there was an eye roll. It only made Dean angrier.

There was an empty field across the street, Dean headed for it.

Once they were out of sight, Dean spun on Sam.

“I’m not going easy on you,” Dean spat.

Sam scoffed. “Ready?”

Dean’s veins were tingling with anger. He was so sick of Sam’s bitchy cocky attitude. Somewhere in the back of his mind, Dean registered this was a bad idea. Alcohol and anger pushed it aside.

He curled his lip in a snarl and nodded. He gave Sam a second before sending a few punches fast and hard at Sam’s jaw and stomach.

Sam blocked and dodged but it kept him on the defensive. It gave Dean a chance to get in close and try to get his arms around Sam’s neck. Sam blocked him, bringing his own arms up and pushing against Dean’s shoulders.

Dean knew he was stronger but Sam was shirtless and Dean’s hands were slipping against his skin. He growled and pulled Sam sideways. They both lost their footing. Dean turned away letting go to catch himself on his hands and knees. Sam still had one foot underneath him facing Dean’s side with one hand on Dean’s shoulders.

With the extra leverage, Sam tried to push Dean over. No way that was happening. Dean spread his knees and dropped lower, making Sam fall on top of him. Dean tried to sit up to throw Sam off. Sam got one knee between Dean’s legs and snaked an arm around Dean’s shoulder from below. Sam held him down and tried to push his arm out of the way.

Dean struggled against Sam’s hold, grunting with effort. Neither of them made much progress. Sam’s thigh was pressed against his ass and Dean could feel Sam’s sweat dripping onto the back of his neck. He knew what they would look like to someone else. It made him irritated and he struggled harder, trying to throw Sam off.

That’s when he felt the line of Sam’s hard cock pressed against his hip.

Dean knew it should probably make him pissed off, or uncomfortable, or something. Something besides relieved. His anger left him so quickly it made him dizzy.

It made him weak too and Sam was able to push one of Dean’s arms out of the way. Sam wasn’t expecting the sudden shift and fell forward on to Dean. Dean used the split second of surprise to roll them both onto their backs. Sam on the ground and Dean on top of him.

In this position, Dean could feel Sam’s cock against his ass now. No way either of them could deny it. Dean stayed like that for a second, both of them trying to catch their breath.

Dean rolled over on top of Sam, propping himself on his arms over him, their legs still tangled together.

Sam was flushed and sweaty, and so damn beautiful. Dean had been trying to ignore it but with Sam below him, hard and panting… Fuck Dean wanted to kiss him.

Sam met Dean’s eyes, seeing the lust there. He must have thought it was anger. “Dean, I-” he swallowed and looked away. “Sorry, it’s not-”

“It’s not what?” Dean shifted his hips, rubbing their cocks together so Sam could feel how hard he was too.

Sam let out a soft moan, biting his lip to try to stifle it. His gaze snapped back to Dean’s face.

Dean didn’t know what he looked like right now but imagined it must be something like a deer caught in the head lights.

Sam didn’t say anything for once, just spread his legs, letting Dean position them better. Dean started moving, pushing his hips against Sam. The pressure and friction felt good, sending shivers of heat down his spine on every thrust. With anyone else, it wouldn’t be enough. Between Sam’s expression and the noises his brother was making, it would be more than enough.

Dean closed his eyes against the pleasure on Sam’s face. It only made him focus on the breathy pants and moans Sam made. The sound went straight to Dean’s cock.

Shit, this was so fucked up.

“Tell me to stop,” Dean murmured harshly.

Sam’s hands found Dean’s forearms, gripping tightly. “Don’t. Please, Dean, don’t stop.” Sam’s voice was all high and whiny. It should be annoying but it really wasn’t.

“Okay, yeah.” Dean ducked, pressing his forehead against Sam’s bare shoulder. He kissed and licked at the skin there to finally get a taste of Sam. The salty sweetness made Dean groan. It was all too much, too much Sam, and Dean knew he wouldn’t last long.

A few more thrusts and Sam’s hands moved to Dean shoulders, fisting in his shirt.

“Yeah, Sammy, come on.” Dean wanted more than anything to watch Sam come beneath him but he couldn’t pull himself away for some reason. Instead, he sucked a mark on Sam’s neck.

Sam bucked up to meet him, shuddering and tensing. “Dean!”

Dean could feel the wetness leak through Sam’s thin shorts onto Dean’s jeans and groaned. He so lost in Sam. His name from Sam’s lips like that echoed through his mind, pushing him over the edge.

“God. Fuck,” Dean panted against Sam’s skin, grinding through his orgasm. “Sammy.”

Sam’s fingers found their way into Dean’s hair and stroked down his back.

Dean let himself relax in Sam’s arms but reality came back eventually. The sticky mess of their pants and a hickey on Sam’s neck a glaring reminder of what had happened.

Dean sat back. Sam had a stupid post orgasm grin on his face but Dean couldn’t get past the guilt in his gut to smile back.

“You can borrow the car Friday," Dean said, standing up.

Sam’s face fell. “What?”

“Sam, you’re a kid. This isn’t- we can’t do this.” Dean tried swallow the lump in his throat.

“But, why not? We both want it.” He sounded hurt, confused.

“It’s wrong, Sam. Let’s just go back to the way it was.” Sam looked like he was going to argue. “Please?”

“Fine.” It was Sam’s turn to push passed Dean, knocking their shoulders hard. “For now.”

 

Win 4

It was obvious Sam didn't want to take no for an answer. For starters, he spent the next six months shirtless as often as he could. He also touched and brushed against Dean as often as possible.

When Dean tried to call him on it he got answers like, “Why bother getting another shirt dirty before school tomorrow?” or “I really had to piss.” Dean didn't want to push it more than that, especially when Dad was around.

The other problem was that part of him liked that Sam was trying to get his attention. Sam did all the time as a kid but when he hit puberty he got all broody. It was nice to feel important to his brother again, even if it was in a way that was illegal in all 50 states.

Dean also couldn't deny it was working. He was pretty sure he didn't jerk off this much even right after he discovered how.

He tried not to think of Sam. It didn't work. His hottest fantasy girl didn't hold a candle to the image of Sam naked and begging to be fucked.

It was somehow so much worse and so much better because Sam knew exactly what Dean was doing the the bathroom. He could probably even guess what Dean was thinking. When Dean walked out of the bathroom after his second shower of the day, Sam would look at him with those knowing eyes and smirk. Dean’s face would heat, from the steam obviously.

So they lived in this highly charged state. Sam waiting for Dean to cave. And really, he was close.

One night, Dean was hanging out, watching a South Park marathon and snorting into his beer. Sam finished his homework and grabbed one of the cans out of the little fridge. When he sat down on the bed, Dean chose not to comment on the alcohol. Sam was nearly seventeen. Dean was younger than that when he started.

They polished off the six pack and the show got a lot funnier. Sam curled up and leaned towards Dean, breathless with laughter. Sam laughing only made Dean laugh harder.

“Dude, it’s not even that funny.”

“I know but-” Sam giggled some more, “I can’t help it.”

“Okay, you are cut off.” Dean reached for his beer on the nightstand across the bed.

Sam went quiet. Dean look down at him and realized their noses were inches apart. Dean inhaled sharply, marveling at the kaleidoscope of Sam’s eyes. He jerked himself away, clearing his throat.

“You’re drunk.” It came out harsher than he meant to.

“If I am then you are too,” Sam said softly.

Dean scoffed, turning back to the TV. “No way. Takes more than a few beers.”

“Me too. I’m not drunk, Dean.”

Something in Sam’s voice made Dean look at him. Sam was staring at him, intent and clear eyed. He folded his knees underneath him and sat up, throwing one leg over Dean’s.

Dean resisted the urge to put his hands on Sam’s hips. Instead, he looked up.

Sam stared back down. “Kiss me.”

“Sam…” Dean choked. It wasn’t that he didn’t want to. They couldn’t.

“Just once. Please?” Sam’s hands balled into fists at his side, betraying his nerves.

Dean sighed, looking away finally. He had to say no and he couldn’t say to that face. Sam knew anyway.

“What if…” Sam took a deep breath. “What if I win?”

Dean let out a surprised laugh. “You want to fight to get me to kiss you?”

Sam sat back on the bed, running a hand through his hair. “Will it work?”

Dean shook his head. He should say no but everyday his resolve crumbled a little more.

Sam took the head shake as a no. “Dean that day in the field. When we.... did that, you never kissed me. Please, just once?”

Dean had never been able to resist those puppy eyes but that didn’t mean he would make it easy for Sam.

“Fine.” Sam’s head snapped up. “If you win.” Sam swallowed.

Dean’s heart was already racing at the thought. “In here though. It’s too cold to go outside.”

“There’s not a lot of room.” Sam pointed out.

Dean shrugged. “We’ll make it work.” He got up and stood between the two beds. “Come here.” He gestured for Sam to stand in front of him. Sam seemed to sense Dean was up to something but didn’t say anything.

“Same rules, ready?” Dean asked once Sam was in place.

Sam nodded and pounced. Dean couldn’t do much without knocking over a lamp or something so he let himself fall. They landed on the bed with their legs still hanging off the edge, Sam on top.

Sam’s face lit up. “Does that mean I win?”

Dean rolled them off the bed and Sam’s back hit the floor. Sam winced.

“Bed doesn’t count,” Dean said.

Dean looked down at Sam. Sam frowned, but for once the little shit didn’t mouth off. He waited for Dean’s next move. Dean could get up, tell Sam no and that’d be it, for now at least. Or…

Dean looked at Sam’s lips, soft and plump, then covered them with his own.

Sam moaned high pitched in the back of his throat, kissing Dean back. Sam clung to Dean’s neck and shoulders, keeping him from pulling away. Dean didn’t want to though.

He got his legs between Sam’s, bending Sam’s knees and pushing them apart with his own thighs. Sam took the hint and wrapped his legs around Dean’s waist. Dean ground his hardening cock against Sam’s ass, pulling another moan from Sam.

“Dean, I want you.” Sam’s eyes were wide and dark, pleading.

Dean groaned. He could easily imagine how hot and tight Sam would feel around his cock. “I know. Me too but, not today, okay?”

Sam pouted. Dean pressed his lips to Sam’s, nibbling at his full lower lip. “You’re not some girl I’m never gonna see again. I wanna do this right.”

Sam nodded. “Okay.”

Dean scooped Sam up, Sam’s legs still around his waist, and stood up. He was heavier than Dean expected, having put on muscle and finally passed Dean in height. Something Dean wouldn’t admit out loud yet. None of it mattered though, Sam was warm and solid in his arms.

Dean dropped Sam on the bed with a bounce. He kissed Sam again, dragging his mouth down Sam’s jaw and swirling his tongue against Sam’s neck. When he reached the line of Sam’s shirt, he sat back.

“Today had to be the day you wear a shirt?”

Sam laughed and tugged the offending article over his head and tossed it to the side. “Better?”

Dean nodded. “Much.”

Sam stopped him. “Wait. What about you?”

Dean looked down at the faded grey fabric. In all Dean’s fantasies, it was Dean getting Sam naked. It was Dean sucking or fingering Sam, making him sweat and moan Dean’s name. Even in his thoughts, Dean had shied away from Sam touching him. It felt more wrong somehow, like Dean was using Sam.

Sam obviously didn’t see it that way.

Dean pulled his shirt off with a cocky smile that he couldn’t make reach his eyes. “There.”

He was back on top of Sam before there could be any more interruptions.

Sam’s hands wandered his chest and back, fingers and nails raising goose bumps. It sent shivers across his body that settled in his cock along with the blood pooling there.

It made it hard to concentrate as he mouthed down Sam’s chest. He sucked Sam’s nipple into his mouth, pressing his teeth down gently. Sam’s fingers flew to his hair.

Dean slid lower, hooking his fingers into the waistband of Sam’s sleep pants and boxers. He tugged them down over Sam’s slim hips, Sam’s cock springing free to lay thick and heavy against his belly. The sight made Dean’s stomach do a little flip. He’d gotten plenty of blow jobs but he’d never given one. He swallowed away the nerves.

A drop of precome leaked from the tip of Sam’s cock and Dean ducked down to lap it up. He swirled his tongue around, licking the velvet soft head into his mouth. He brought his hand up around the base and sucked hard. It earned a moan and another spurt of precome, sweet across his tongue.

Sam ran his hand through Dean’s hair, drawing Dean’s eyes up to his, Dean’s lips still wrapped around Sam’s cock.

“Fuck, Dean. Just seeing you like that is gonna make me come.” Sam dropped his head back on the pillow, still idly twirling his fingers through Dean’s hair.

Dean pulled off. “So watch,” he murmured.

He sucked Sam down as far as he could without gagging, pushing his tongue against the underside. He bobbed his head and hollowed his cheeks. When he flicked his eyes up again, Sam was watching him. Dean could see his breath leaving him in shaky gasps.

Dean kept going, working his hand over the part his mouth couldn’t reach. His cheeks ached and his lips felt numb. It was worth it for porn star noises he earned from Sam. It made Dean’s cock throb against his leg but he ignored it for now.

“Oh God, Dean,” Sam groaned. “I’m so close. I’m gonna come.” Sam moved his hand, giving Dean space to move. Dean didn’t want to though.

He sucked harder, bobbing his head faster, adding a twist at the end like he’d seen a girl do in a porn. Sam seemed to like it, letting out frantic little ahs.

Sam went silent when his orgasm hit. Dean gagged on the come hitting the back of his throat but he swallowed it down. He slowed his movements and let off the suction. He worked Sam through till he was lapping slowly over Sam’s cock from base to tip, getting every single drop.

Dean kissed up Sam’s body till he was leaning over him again. Sam had a sleepy, sated look on his face but grinned. He wrapped his arms around Dean’s neck and pulled Dean down for a kiss. He licked into Dean’s mouth and moaned at the taste of his own come.

The noise called Dean’s attention to his own insistent need. Sam looked too tired to reciprocate though and Dean still wasn’t sure he even wanted him to. He had decided to take care of it himself when he felt Sam’s hand cup him through his pants.

Dean breathed through his nose heavily. Sam pulled back to check Dean’s expression and seemed satisfied with what he saw.

“You don’t-Fuck” Dean broke of into a moan when Sam pressed against the head of his cock. “You don’t have to.”

“Stop being so noble and shut up. I want to, Dean.” Sam pressed down again and ran his fingers over the length. Dean couldn’t help pressing into Sam’s hand. “You want it too.”

Dean panted, heat gathering at the base of his spine. He couldn't exactly deny it.

“Switch places with me,” Sam murmured.

Dean bit his tongue on a whine when Sam moved his hand to push himself up.

Once Dean was on his back, Sam wasted no time freeing Dean’s cock and sucking it down like a pro.

“Fuck, Sammy. You done this before?” The question was out before Dean realized he may not want to know. He knew Sam had fooled around with girls. It didn't cross his mind till that moment, he may have fooled around with guys too.

He was worried for nothing.

“No. I just. Have wanted.” Sam spoke between kisses and licks to Dean’s cock. “To do this. For so long.” Sam swallowed Dean down again.

Dean groaned as the wet heat of Sam's mouth enveloped him. It felt incredible. He balled his hands into fists to keep from bucking his hips and choking Sam. Sam sucked hard, like he was trying to suck Dean’s brains out through his dick. He might have succeeded since all thoughts that weren’t about his dick or Sam’s mouth had left Dean’s head.

Sam paused and looked up through his bangs. Dean panted and gasped in frustration.

“Does that feel good?” Sam asked earnestly. It wasn’t a coy attempt at dirty talk.

Dean brushed Sam’s hair out of his face. He tried for gentle even though his reptilian brain wanted to pin Sam down and fuck him hard. “Yeah, Sammy. Feels awesome. Don’t stop, please.”

Sam ducked his head again, bracing himself low, his fingers tickling under Dean’s hip bones.

Sam didn’t stop again till Dean came, his vision going white, ears ringing and toes tingling. Sam swallowed every drop, moaning like it was the best thing he’d ever tasted.

Dean laid there panting, blood slowly returning to the rest of his body.

Sam crawled up to rest his head against Dean’s chest. He traced patterns over Dean’s skin Dean curled an arm around Sam and breathed a contented sigh.

He didn’t feel as bad as he thought he would. There was still that voice in the back of Dean’s head calling him hateful names. With Sam warm against him, it was easy to ignore.

 

Win 5

The next year was the happiest Dean could remember.

They had to hide their relationship from Dad and the rest of the world.

They didn't have much time with each other. Sam was nearly 18 so Dean went with John more often than he stayed home. A couple days or a couple hours, it didn’t matter. Whatever time they were able to steal for the two of them, they spent lost in each other.

Dean still insisted they wait for “real” sex. They had all the time in the world, he’d assumed.

Dad kept talking about the three of them hunting together full time once Sam finished school. Dean hoped, even though it made his gut clench with guilt, that Dad would go off on his own more. Dean could picture a life where Sam and him hunted side by side. They would go back to cheap motels at night and (Dean rolled his eyes at himself for being cheesy) make love till they were both exhausted.

Sam apparently had other ideas.

Dean really hadn’t been snooping. He was just looking to steal a pair of clean socks from Sam’s duffel. The envelope was barely covered at the bottom of the bag.

Dean dug it out and read it. Accepted to Stanford, full ride.

Dean’s breath left him and his chest ached. He sat on the bed when his knees gave out. He knew Sam wanted normal but… Dean was never going to be normal. Their relationship was sure as hell never going to be normal. Besides, Sam had to know Dean couldn't abandon Dad.

Anger flared hot in his belly, burning away anything else.

When Sam came home, it only took one look at Dean for him to realize something was wrong.

“This family not good enough for you?” Dean spat, throwing the letter at Sam’s chest.

Sam caught it, but didn’t need to look at it to know what it was.

“Dean, wait. I wanted you to come with me. They have-” Sam started.

Dean scoffed. “Sam, I’m not gonna fit into your apple pie life. I thought-” Dean cut himself off. It didn’t matter what he thought. “Never mind. ” He head for the door, intending to brush passed Sam.

His brother caught the front of his jacket and spun Dean to face him. He wound his arms around Dean’s neck and buried his face against Dean’s shoulder.

“You are my life. Come with me, get a job. We can leave this whole mess behind. No one there will know we’re brothers.”

Dean shoved Sam away. “And what about Dad? Without back up he could get killed. Is that what you want? What about the thing that killed mom? What about the people we help?”

Sam looked away. “It’s not our problem. It doesn’t have to be our fight. There are other ways to help people.”

Dean stared at Sam, frowning. “Who are you? This is what we do, Sam!”

Sam still wouldn’t look at him. “I don’t want to do this Dean. I’ve never wanted to do this. I thought you understood that.” He sounded hurt.

Yeah, well, Dean was hurting too. “And I thought you’d gotten over it!” he yelled. Dean shook his head. He couldn’t believe this was happening. “Guess it doesn’t matter. Have fun at school, college boy.” Dean said the last two words with as much derision as he could.

He turned to leave but felt Sam’s hand on his arm. “If- If I win, will you come with me?”

Dean spun on him. “You’re gonna pull that now?”

Sam’s eyes sparkled with unshed tears. He nodded.

“Fine. But this is for real.”

Dean found a spot out of sight for them to face off. They stood facing each other, Dean felt like he could barely recognize the man in front of him.

Dean cocked an eyebrow.

Sam nodded.

Dean punched him hard in the jaw.

Dean didn’t think it was hard enough to crack or dislocate anything, but it would leave a dark bruise the next day.

Sam staggered back holding the side of his face. The tears finally leaked down his cheeks. Dean wanted to feel bad. He wanted to fall on his knees and beg for forgiveness, kiss away Sam’s pain and make everything better. But then he remembered the letter and hardened his heart.

Dean hit Sam again, this time in the stomach. Sam doubled over coughing.

“Come on, dude. You’re not even trying,” Dean taunted, spreading his arms. “Were you only pretending you gave a shit?”

Sam straightened. He fainted at Dean’s stomach with his left and connected with the side of Dean’s head hard with his right.

The skin split and Dean could feel blood start to spread across his face. It stung like all hell.

“There ya go. I knew you were better than that.”

Sam swung again but Dean dodged.

Dean got another hit in on Sam’s stomach. When Sam doubled over, Dean kicked his legs out from under him and threw him to the ground.

Sam landed on all fours.

“Dean, please?”

Dean’s hands shook. He wanted to lash out, to kick and punch and scream until there was nothing left of either of them and terrible pain in his chest wasn’t there.

He didn’t do it though, and he knew he didn’t even really want to.

Dean put his foot against Sam’s side a shoved. Sam fell to his side and rolled onto his back.

“Please?” Sam begged again.

Dean turned and walked away.

From then on, Dean hunted by himself. He could have told Dad about the letter. Dad would have put a stop to it, but Dean didn’t want to force him to stay.

Dean avoided Sam as best he could for the next month till graduation. He had to see him a couple times. Once when dad came back to discuss plans, plans Dean and Sam both knew would fall through. The second time, to watch Sam say goodbye, or at least as close as he could get to it with Dad.

Sam was 18 and graduated. He was leaving. Dad couldn’t stop him.

He tried.

He yelled and raged and even guilted. Sam gave it all right back though. As usual, Dean was in the middle, only he wasn’t really anymore. There was no middle, just him and Dad. Sam was on his own.

Dad got in his truck and drove off eventually, leaving Dean and Sam staring at each other in the rainy street.

“I miss you,” Sam said to his feet, barely louder than the rain.

Dean couldn’t hide the pain on his face and was glad Sam was looking away.

“Will you visit?” Sam asked when Dean didn’t say anything else.

“No. Goodbye Sam.”

 

Lose

Dean couldn’t stay away from Sam for long.

Around Christmas, he managed to find a case in California. After taking out the poltergeist, he swung by Stanford. He got Sam's address from the registrar by sweet talking the woman behind the desk.

Sam wasn't expecting him. He’d picked out a present to surprise Sam with by way of apology… and maybe more. He waited for Sam outside, getting side eyed by the kids playing Frisbee and studying.

When Sam finally showed, he was surrounded by a group of friends, laughing and joking. He looked relaxed, more happy than he ever was with Dean. He looked like he belonged.

Dean stared for a moment. He couldn’t take that away. It’s all Sam ever wanted. He ran.

He ran back to the car and sat behind the wheel shaking and fighting back tears. He’d been so broken these past few months, he didn’t think it was possible to feel worse. Seeing Sam like that though…

Dean thought Sam would be as hurt and aching as he was. He thought what they had was important to Sam. It never crossed his mind that Sam could move on. That maybe it was a teenage crush for him.

Or that he could hurt more than he already did.

Dean pulled the silver ring out of his pocket. It was a peace offering, a compromise. Maybe they could find away to have it. God knows if anyone could, it was them.

But Sam didn’t want it.

Dean put the ring on his own hand instead, a reminder not to get too attached to anyone, even family, and drove off.

***

Fours years later, Sam had left school and returned to hunting. Jess was dead. Dad was dead. And the thing that killed them was still alive.

It should be a grim time, and it was, but Dean couldn’t help but be glad to have his little brother by his side again. Sam was a pain in the ass, shit talking and treating Dean like he was an idiot. But that was Sam. It was everything Dean loved.

Dean fiddled with his ring, trying to not let himself think of the way they had been. Sam never brought it up. They both pretended like it never happened, any of it. Sometimes though, Sam would look at him, with that beautiful dimpled smile and mischief in his eyes, and part of Dean would melt.

One night after a particularly brutal hunt, they were both bruised and exhausted. They lay there but sleep refused to come. Sam crawled into his bed, tucking himself against Dean’s back like he used to.

Dean wanted to send him away. It hurt too much to have Sam this close and know that Sam didn’t feel the way he used to. Maybe he never felt that way at all. Dean didn’t send him away though and soon the extra warmth relaxed tired muscles and they both fell asleep.

Dean woke up with Sam wrapped around him. He could feel Sam’s erection pressed against his hip. Sam’s hot breath brushed his neck, sending unwanted quivers down his spine. It wasn’t Sam’s fault though. Sam was still asleep.

Dean tried to slip out of bed without waking him but Sam’s eyes snapped open as soon as Dean shifted. When Sam registered what woke him up, a happy grin spread across his face and he relaxed and snuggled closer.

“Sam,” Dean said, his voice hoarse.

“Mmm?”

Dean tried to shift out of Sam’s grasp. “We can’t do this.”

Sam didn’t loosen his grip. “Why? Don’t give me that it’s not right bullshit again.”

“I can’t.” Dean winced at the broken sound of his own voice.

Sam let go and sat up. Dean scrambled out of bed and into the bathroom. He brushed his teeth and showered, taking as long as he could. He hoped Sam would have food and coffee when he got out. They could continue on with the day pretending nothing happened.

He got half of it. Sam ran across the street to get coffee and donuts but he was unusually quiet for the card ride to nowhere. He picked at his salad when they stopped for lunch and only glanced half through the local newspaper.

Dean knew the night would be uncomfortable. He kept driving till Sam fell asleep against the window. When he couldn’t keep his eyes open anymore, Dean finally pulled into a motel and got them a room. He hoped that Sam would be too tired to talk.

He wasn’t though.

“What do you mean you can’t?” Sam said finally as they lay in separate beds staring at the ceiling.

Dean didn’t answer.

“I know you’re not asleep,” Sam snapped.

Dean sighed impatiently. He was tired and he didn’t want to have this conversation. “I meant there are a million reasons us fucking is a bad idea, Sam. One, we’re brothers. And B, I don’t want to.”

Sam scoffed. “Bullshit.”

“What?” Dean felt a familiar and dangerous anger start to burn through his veins.

“Bull. Shit. It didn’t matter that we were brothers for a whole year. Why would it matter now? And I see the way you look at me, Dean. You want this as bad as I do. You’re just being stubborn.”

“Wow. What did those frat guys teach you? Should I sleep with mace under my pillow?”

“That’s not- No! I know you Dean. And I know that look. I thought we needed sometime and eventually we’d… last night…” Sam trailed off.

“We’d what? We’d kiss and ride off into the sunset for our happily ever after? You tried happily ever after, look where that got you.” Dean flinched, glad Sam couldn’t see him in the darkness. He hadn’t meant to bring up Jess, even indirectly.

Sam was silent for awhile, long enough Dean thought he might have gone to sleep.

“I wasn’t happy with Jess, you know." Dean wanted to scoffed but he stayed silent. "I was living, getting by, content. But not happy. It’s what eats me up, Dean. It’s why I need revenge so bad. Even with everything I couldn’t tell her, she loved me. Even though she knew my heart belonged to someone else.” Sam sniffled. “She deserved so much better.”

Dean sighed. “We’ll get Yellow-Eyes. We’ll do right by her and Mom and Dad and everyone else. We’ll figure it out.”

“Yeah, I know.”

There was another long stretch of silence before Sam spoke again.

“I was happy with you, Dean. That year was the happiest of my life. Even with dad and hiding and changing schools all the time, I was so fucking happy.”

Dean wanted to scream, then why did you leave? Instead he rolled over and muttered, “go to sleep.”

“Weren't you happy? Why don’t you want that again?”

Dean groaned in frustration. “Can’t you shut up about this? Take a hint, will you? It’s not gonna happen.” His eyes burned and he wanted to be asleep already.

Sam sat up and flicked the lights on. “But why not?”

“Because I can’t lose you again!” Dean yelled, sitting up to glare at his brother.

Sam looked like he’d been kicked in the stomach. All his breath left in a rush. He started to get up.

“If you so much as lay a finger on this bed, I will deck you, Sam. You know I will.” Dean absolutely meant it.

“Dean…”

“Don’t. We’re done talking about this.” Dean reached over and turned off the light. “Goodnight.” He turned away from Sam.

Sam sighed and Dean could hear the covers move as he got back in bed.

Dean laid there, emotions too high to fall asleep.

“What if I win?” Sam’s voice was small, like he wasn’t sure he wanted Dean to hear, like he was afraid of Dean’s reaction.

Dean closed his eyes against the pain of the night that followed the last time Sam had said that.

Dean rolled onto his back. “If I beat you, will you let it go?”

“For now.”

“No. Forever.” He didn’t want to have this fight over and over.

Dean could hear the click of Sam’s throat as he swallowed nervously. “Fine.”

Dean sat up and turned on the light, rubbing his face. “Let’s get this over with.”

“Outside or inside?” Sam asked swinging his legs off his bed.

It was too damn cold outside. Dean glanced around the room. There was an open space by the door. It would have to do.

Dean got up and stood in the space. “Here,” he grunted.

Sam looked around, getting his bearings and shaking his arms and shoulders out.

Dean crouched into a defensive position before asking, “ready?”

Sam nodded.

This fight went a lot like the one in Sam’s apartment except the light was on and they knew who they were fighting. They dodged around the furniture, trading blows only hard enough to leave faint bruises.

Sam was three inches taller and twenty pounds of muscle heavier. Dean had to work to keep out of his reach. Something about it was familiar and exhilarating all at once.

The gleam in Sam’s eye and his hectic grin tugged at Dean’s heart. The clashed, coming together to struggle for dominance. Sam's nearness started to make Dean wonder if he really wanted to win. Forever was a long time not to forgive his beautiful baby brother.

When Dean got distracted by the gleam of sweat on Sam’s throat, Sam swept his feet out from under him. Dean landed flat on his back on the dirty carpet.

Dean lay there in stunned silence. Sam offered a hand to help him up and Dean took it hesitantly, but Sam released him as soon as Dean was on his feet.

“So what happens now?” Dean muttered not meeting Sam’s eyes.

“Nothing.” Sam sighed. “I don’t want to force you into something, Dean. I hurt you too. We’ll keep going like we were. Pretend that tonight and that year never happened.”

It felt like Pandora’s box had been opened though. It had taken Dean years to build those walls and Sam was telling him to put them back overnight. Not to mention, Dean wasn’t sure he wanted them back.

“What if we…” Dean rubbed the back of his neck and met Sam’s eyes. He dropped his hand. “I could kiss you instead. If that’s what you want.”

Sam’s eyes flew to Dean’s mouth and Dean realized he licked his lips unconsciously.

“Is that…” Sam cleared his throat. “Is that what you want?” Sam asked thickly.

Dean grabbed Sam’s neck and pulled him down till their lips met. He was done talking.

Sam hesitated for only a second. His lips moved against Dean’s, hard and demanding and his tongue invaded Dean’s mouth. Sam’s huge hands landed on Dean’s waist, pulling their hips together. One hand held Dean firmly in place and the other came up to cup Dean’s cheek.

With Dean’s arms angled up to reach around Sam’s neck, he felt small. Sam had gotten taller and broader since the last time they’d done this. It was at once irritating and really fucking awesome.

“Do you have any idea how much I’ve missed this?” Sam mumbled against Dean’s lips.

Dean licked into his mouth and tugged Sam’s top lips against his teeth. He brought his hand down Sam’s chest to cup his growing erection.

Sam groaned. “Fuck, Dean. Is this okay? We don’t have to…you know, right away. We can go slow.”

With Sam talking, Dean moved to sucking at his neck. “Fuck going slow.” As kids, Dean thought they had forever. Now he knew better. He met Sam’s gaze with serious eyes. “I want you.”

Sam shuddered. “Yeah. Yeah, okay.” He pulled Dean’s lips back to his and turned to back up against one of the beds.

Dean followed, breaking apart only long enough to let Sam slide to the middle of the mattress. Sam spread his legs easily, letting Dean slot between them. Their sleep pants and boxers were a flimsy barrier between the heat of their bodies. Dean rutted against Sam, rubbing their cocks against each other. The pressure sent shivers over Dean’s body on every thrust.

Sam pushed at Dean’s pants, tugging them over the curve of his ass. “Come on, please. I’ve waited so long.”

Dean stopped to catch his breath, trying not to think about what they were about to do. Not only was he afraid the thought might make him lose it too soon but he didn’t want to overthink it. “Okay,” he muttered pulling his shirt over his head and shimmying out of the sleep pants. Sam did the same below him.

When they came together again, all heated skin against skin, Dean couldn’t help the moan that escaped him. Sam couldn’t either. Dean ran his hand over the well defined muscles of Sam’s stomach. He bit his lip on a cheesy comment and marveled at Sam’s beauty a moment before capturing Sam’s mouth for a kiss.

Sam’s hands explored Dean’s back, sliding down to his ass and around before finally gripping his cock tight. He gave one firm stroke. Sam’s thumb spread a blob of precome around the tip. He broke the apart long enough to lick his thumb clean, making their next kiss taste like Dean.

Dean was distracted by Sam’s pornstar moves and the feel of their tongues against each other. He didn't notice what Sam’s hand was doing between them.

Dean sat back and looked between them. Sam reached past his balls to circle around his hole, one finger pressing into the first knuckle.

Dean groaned at the sight. “Fuck Sammy, that’s...” A thought occurred to Dean and, even if he wasn’t sure he wanted the answer, it kind of mattered this time. “Have you done this before?”

“Yes, but not exactly…” Sam said evasively.

Dean frowned. “What does that mean?”

Sam frowned right back. Clearly annoyed at having this conversation now. “I’ve used toys before okay?”

Ridiculously, Dean felt himself blush. “Okay. I just didn’t want to hurt you.” Dean cleared his throat. “We’ll need lube and a condom.” Dean got up to dig the items out of his bag.

“Are you-” Sam bit his lip. “I mean, I’m clean. You don’t have to use a condom… if you don’t want.”

Dean made a low guttural noise and his cock twitched. He dropped the pack of condoms back in the bag, and climbed back onto the bed, bottle of lube in hand. He leaned over and kissed Sam. “God, I’ve wanted to feel you on my cock for so long.”

Dean propped himself on one elbow. With the bottle in his left hand he pour some lube across the fingers of his right. He brought them between Sam’s legs to his entrance, watching Sam’s face as he circled and pushed one finger inside.

Sam moaned and clenched down at the intrusion. Dean kissed his shoulder. “Gotta let me in, Baby Boy.”

Sam moaned again at the old nickname. He breathed deeply, trying to relax.

Dean worked him open slowly, watching Sam’s face every time he added another finger. Dean didn’t realize how much he missed the way Sam looked all desperate and needy like this.

Dean was achingly hard by the time he could fit three fingers into Sam.

“Dean, I’m ready. Please, just fuck me,” Sam begged for at least the third time.

Dean pressed his teeth into Sam’s shoulder, trying not to come from Sam’s voice. “Gonna fuck you good and hard. Wanna make sure you’re all stretched out for me.”

Sam whimpered and bucked his hips against Dean’s fingers. “Please.”

Dean pushed his fingers against Sam’s prostate, making him writhe and moan, and then pulled them out. “Alright, you’re ready.”

Dean moved from where he’d been lying along Sam’s side to between his legs. Sam bent his knees pulling them up towards his chest to give Dean better access. Dean stared down at Sam’s hole all slick and twitching, and his cock throbbed in response.

“Fuck, Sam. I don’t think I’ll last long,” Dean said as he slicked his cock.

“It’s okay. Me either,” Sam panted.

Dean lined himself up. He looked up at Sam. “Ready,”

Sam nodded, teeth making white crescents against his lower lip.

Dean pushed his hips forward till the head of his cock slipped inside. Sam was hot and tight and soft and Dean wanted nothing more than to bury himself to the hilt. He held there though.

“Okay?” Dean grunted.

“Yeah. Keep going.”

Dean slid in, watching Sam’s face for signs of pain until his hips were flush against Sam’s ass. He dropped his head to crook of Sam’s neck.

“God, you feel amazing. Fucking perfect,” Dean whispered.

Sam clenched around him and Dean gasped, grinding his hips into Sam.

Sam shifted and writhed, riding Dean’s cock from underneath.

Dean groaned and started to match Sam’s rhythm. It had to be the best thing Dean had ever felt. No girl had ever matched the way Sam seemed to fit him to perfectly. And Dean knew he had never been this turned on before.

Dean could feel his body building toward its peak. He wrapped his hand around Sam’s cock and stroked it in time with his thrusts.

“Gotta come for me Sammy. Not gonna last much longer.”

“I’m close Dean. Fuck.” Sam bucked up into Dean’s grip, matching Dean’s thrusts and panting.

“Come on. Wanna feel you come on my cock. I’ve wanted it for so long. Come on.” Dean babbled nonsense against Sam’s ear trying to hold off as long as he could.

Inevitably, he could feel that edge approaching and Dean moaned Sam’s name when he finally fell over it. He felt Sam tighten around him a second after, his come leaving warm white streaks across them both.

Sam’s hands slid up and down Dean’s arms as they lay there catching their breath, sweat cooling on their skin. Dean felt like he should say something but he didn’t know what. The lack of sleep finally caught up to Dean and he nearly passed out on top of Sam.

Sam patted his arm. “Let me up.”

Dean rolled over, still half asleep.

He woke up to a damp cloth landing on his stomach. He grunted but at least it was warm.

He wiped himself off as Sam climbed naked into the clean bed. Once he was clean, he chucked the towel back into the bathroom. He was more awake and wasn’t sure if he should join Sam in the other bed.

Sam made the decision easy.

“There’s lube and come all over those sheets. Come over here.”

Dean grumbled like it was a hassle but he was glad. This was getting weird and he didn’t know how to fix it.

He crawled into bed with Sam and Sam snuggled up against him like he used to when Dad was gone. It felt painfully familiar. Dean turned off the light.

He ran a hand through Sam’s sweat damp hair and let out a shaky breath.

“I won’t leave again Dean,” Sam said. He met Dean’s eyes. “I promise. I don’t ever want to live without you, without us, again.” He laid his head back down against Dean’s chest. “I love you,” Sam murmured.

Dean swallowed past the lump in his throat. He stroked Sam’s hair again, giving it a tweak. "Girl."

Sam let out a short laugh and pressed his lips to Dean's side.

On Dean's other hand, he still wore the ring he’d bought for Sam all those years ago. He thought about someday explaining it to Sam, telling Sam about his visit to Stanford. He resolved to give it to him someday. Preferably in a church.

Sam’s breathing evened out into sleep.

“Me too, Sammy,” Dean finally answered.


End file.
